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When Crisp was a child, his great-grandmother Wilda Smith referred to him a "Co," which was short for his first name, Covelli. His sister Sheileah and his godbrother Marcus, inspired by Cocoa Crispies Cereal, began referring to him as "Coco," and the nickname stuck.

Crisp was also a part of the RBI (reviving baseball in inner cities) program, where he played third base. He is one of eight RBI League alumni to have reached the majors, and was inducted into the RBI League Hall of Fame in 2006.

Crisp became the starting center fielder with the Indians in mid-2002, replacing the injured Matt Lawton. For the next few seasons, Crisp established a reputation as an excellent fielder and speedy baserunner. Despite his success, Crisp had to fight for his roster spot each spring. In 2005, Crisp moved to left field following the emergence of another young outfielder, Grady Sizemore. In his final two seasons with the Indians, Crisp showcased his offensive talent by batting .297 and .300 with 31 total home runs and 35 steals.

After Johnny Damon signed with the New York Yankees, the Red Sox sought Crisp to fill Damon's vacated role both in center field and as a lead-off hitter. In January 2006, the Red Sox sent prospect third basemanAndy Marte, pitcherGuillermo Mota, catcherKelly Shoppach, a player to be named later (Minor Leaguer Randy Newsom), and cash considerations to the Indians for Crisp, catcher Josh Bard and pitcher David Riske. Crisp, already a fan favorite in Cleveland, saw his national fame jump dramatically upon entering big-market Boston before playing a single game in a Red Sox uniform.

After a promising start to his Red Sox career, which included signing a 3-year contract extension worth $15.5 million, Crisp broke his left index finger attempting to steal third base and spent the next 42 games on the disabled list. After returning to the Red Sox outfield on May 28th, Kevin Youkilis had taken over the leadoff spot, and Crisp usually batted 7th or 8th in the line-up for the rest of the year. In 105 games, he had a .264 batting average with 8 home runs and 36 RBIs. Besides his injury, Crisp's 2006 season may be best remembered for a fantastic defensive catch against the New York Mets on June 29th.

Crisp began the 2007 season struggling offensively. On April 20, 2007, Crisp fell over a short wall at Fenway Park while trying to catch a home run by Alex Rodriguez. Although he was unable to make the catch, missing by inches, he hit a game tying triple off of Mariano Rivera in the bottom of the eighth. The Red Sox went on to win 7-6. During this season he made numerous impressive catches in the outfield. It has even been claimed by one major league club that Crisp is easily the best defensive center fielder in all of Major League Baseball.[1] Although he has struggled at the plate throughout much of the season, between June 13 and July 5, Crisp raised his batting average from .221 to .265, and after a 3 for 4 game on July 22nd he raised his average to a season high .277. On June 18th, entering the game with only two home runs in the season, Crisp belted two homers in his first multi-HR game of his career in a 9-4 loss to the Atlanta Braves.

On August 5, Crisp was almost run over by the Seattle Mariners' mascot, the Mariner Moose. The Moose, driving a lap around Safeco Field's warning track, nearly collided with Crisp as he was leaving the dugout for his position in the middle of the fifth inning; Crisp had to jump out of the way to avoid being hit. Red Sox pitching coach John Farrell was incensed by the mascot's actions and voiced his displeasure to both the mascot and Seattle's head groundskeeper. Immediately following the incident, the Red Sox received an apology from Mariners GM Bill Bavasi.[2]

On October 21, in game 7 of the American League Championship Series, Crisp made the catch that sent Boston to their second World Series in four seasons. He sprinted over to the triangle in center field and collided with the wall after making the catch.

Although he was the team's starting center fielder throughout the 2007 season, he was benched mid series during the ALCS for rookie Jacoby Ellsbury. He remained benched for the 2007 World Series, only appearing late in games for defensive substitutions.